I think it's most constructive to establish the differences in people's expectations and their norms, because these are very different from one person to the next. One person might expect an amp to be as accurate as possible, and the other as musical as possible, most people I wager are somewhere in between - these are not the same expectations and one is not more correct than the other. This is why a DAC like Benchmark is awesome for some but not others.
In this context I feel that modern electronics has made *great* improvements over previous generation products, not because it does any one thing better, but that consumers have ever so many choices to find exactly what they want to fit their different expectations.
Back in the day, if you didn't care for the tube sound, you were out of luck. Modern electronics affords you not only the choice of "steril" solid state versus "luscious" tube, but all shades in between. You can now have a "solid state sounding tube amp", or a "warm sounding solid state amp". To someone whose audio enjoyment is most ably fulfilled by a 90's era Rotel, then no other piece of equipment is going to bring about greater satisfaction. Now, in case that 90's era Rotel was only deliver 95% of maximum enjoyment, then the variety of modern electronics greatly increases the chance that the listener will find something that gets closer to 100%.
I guess my answer to the $300-vs-$1000 question is, you get out of it whatever your ears tell you. If $300 bought you the best amp to your ears, even a $100,000 amp isn't going to rock your world any harder. If you do find a $1000 amp that sounds better to you than a $300 amp, that's just how the dice rolled and you need to decide whether you want to part with the extra $700.
Jack